Chinese Journal of Organic Chemistry >
Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine
Received date: 2021-01-25
Revised date: 2021-02-21
Online published: 2021-03-12
Supported by
National Natural Science Foundation of China(21772078); Fundamental Research Funds for the Central Universities(2682019CX70); Fundamental Research Funds for the Central Universities(2682019CX71); Fundamental Research Funds for the Central Universities(2682020CX55); Program of Natural Science Foundation of Xinjiang Autonomous Region Colleges (Key Program)(XJEDU2018I018)
Dendrobine is an important sesquiterpenoid alkaloid bearing the picrotoxane carbon skeleton isolated from the traditional Chinese medicine “Chin-Shih-Hu”. Because of structural characteristics of fused polycyclic and seven contiguous stereocenters, and exhibiting analgesic, antipyretic activities, dendrobine has attracted a great deal of attentions from both synthetic organic chemists and medicinal chemists. Over the past 50 years, there has been a number of research reports on the pharmacological activities and chemical synthesis of dendrobine. This review summarizes the biosynthetic hypothesis and synthetic advances on dendrobine.
Key words: natural product; sesquiterpenoid alkaloid; dendrobine; total synthesis; picrotoxane
Jian Xiao , Yu Peng , Wei-Dong Z. Li . Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2636 -2649 . DOI: 10.6023/cjoc202101041
| [1] | Pharmacopoeia Committee of Ministry of Health, Chinese Pharmacopoeia, 2005 Edition I, Chemical Industry Press, Beijing, 2005, p.62 (in Chinese). |
| [1] | (中华人民共和国卫生部药典委员会, 中华人民共和国药典2005年版一部, 化学工业出版社, 北京, 2005, p. 62.) |
| [2] | (a) Suzuki, H.; Keimatsu, I.; Ito, K. Yakugaku Zasshi 1932, 52,1049. |
| [2] | (b) Suzuki, H.; Keimatsu, I.; Ito, K. J. Pharm. Soc. Jpn. 1934, 54,802. |
| [3] | (a) Chen,K. K.; Chen,A. L. J. Biol. Chem. 1935, 111,653. |
| [3] | (b) Chen,K. K.; Chen,A. L. J. Pharmacol. 1935, 55,319. |
| [4] | (a) Inubushi, Y.; Sasaki, Y.; Tsuda, Y.; Yasui, B.; Konita, T.; Matsumoto, J.; Katarao, E. Nakano, J. Yakugaku Zasshi 1963, 83,1184. |
| [4] | (b) Yamamura, S.; Hirata, Y. Tetrahedron Lett. 1964, 5,79. |
| [4] | (c) Onaka, T.; Kamata, S.; Maeda, T.; Kawazoe, Y.; Natsume, M.; Okamoto, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1964, 12,506. |
| [4] | (d) Huang,W. -K. Acta Chim. Sinica 1965, 31,333 (in Chinese). |
| [4] | ( 黄文魁, 化学学报, 1965, 31,333.) |
| [4] | (e) Guo, L.; Frey, W.; Plietker, B. Org. Lett. 2018, 20,4328. |
| [5] | (a) Okamoto, T.; Natsume, M.; Onaka, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1966, 14,672. |
| [5] | (b) Morita, H.; Fujiwara, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56,5801. |
| [5] | (c) Meng,C. -W.; He,Y. -L.; Peng, C.; Ding,X. -J.; Xiong, L. Fitoterapia 2017, 121,206. |
| [6] | (a) Li, R.; Liu, T.; Liu, M.; Chen, F.; Liu, S.; Yang, J. J. Agric. Food Chem. 2017, 65,3665. |
| [6] | (b) X,Y. -Y.; Xu,Y. -S.; Wang, Y.; Wu, Q.; Lu,Y. -F.; Liu, J.; Shi,J. -S.. J. Pharm. Pharmacol. 2017, 69,1409. |
| [6] | (c) Song,T. -H.; Chen,X. -X.; Lee,C. K.-F.; Sze,S. C.-W.; Feng,Y. -B.; Yang,Z. -J.; Chen,H. -Y.; Li,S. -T.; Zhang,L. -Y.; Wei, G.; Shi, J.; Xu, K.; Ng,T. -B.; Zhu,L. -L.; Zhang,K. -Y. Phytomedicine 2019, 53,18. |
| [7] | (a) Cross,A. D. Rev. Chem. Soc. 1960, 14,317. |
| [7] | (b) Kolbe, M.; Westfelt, L. Acta Chem. Scand. 1967, 21,585. |
| [7] | (c) Kolbe-Haugwitz, M.; Westfelt, L. Acta Chem. Scand. 1970, 24,1623. |
| [7] | (d) Yamazaki, M.; Matsuo, M.; Arai, K. Chem. Pharm. Bull. 1966, 14,1058. |
| [7] | (e) Biollaz, M.; Arigoni, D. J. Chem. Soc.,Chem. Commun. 1969,633. |
| [7] | (f) Arigoni, D. Pure Appl. Chem. 1975, 41,219. |
| [7] | (g) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,171. |
| [7] | (h) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,824. |
| [7] | (i) Corbella, A.; Gariboldi, P.; Jommi, G. J. Chem. Soc.,Chem. Commun. 1973,729. |
| [7] | (j) Corbella, A.; Gariboldi, P.; Jommi, G. Sisti, M. J. Chem. Soc.,Chem. Commun. 1975,288. |
| [7] | (k) Cordell,A. G. Chem. Rev. 1976, 76,425. |
| [7] | (l) Li, Q.; Ding, G.; Li, B.; Guo,S. -X. Sci. Rep. 2017, 7,316. |
| [8] | (a) Yamamoto, K.; Kawasaki, I.; Kaneko, T. Tetrahedron Lett. 1970,4859. |
| [8] | (b) Kende,A. S.; Bentley,T. J.; Mader,R. A.; Ridge, D. J. Am. Chem. Soc. 1974, 96,4332. |
| [8] | (c) Hu,Q. -Y.; Zhou, G.; Corey,E. J. J. Am. Chem. Soc. 2004, 126,13708. |
| [9] | Yamada, K.; Suzuki, M.; Hayakawa, Y.; Aoki, K.; Nakamura, H.; Nagase, H.; Hirata, Y. J. Am. Chem. Soc. 1972, 94,8278. |
| [10] | (a) Mori, M.; Uesaka, N.; Shibasaki, M. J. Org. Chem. 1992, 57,3519. |
| [10] | (b) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F. Chem. Lett. 1993,213. |
| [10] | (c) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59,5633. |
| [10] | (d) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992,443. |
| [10] | (e) Cassayre, J.; Zard,S. Z. J. Am. Chem. Soc. 1999, 121,6072. |
| [11] | (a) Lee,C. H.; Westling, M.; Livinghouse, T.; Williams,A. C. J. Am. Chem. Soc. 1992, 114,4089. |
| [11] | (b) Lee, Y.; Rochette,E. M.; Kim, J.; Chen,D. Y.-K. Angew. Chem.,Int. Ed. 2017, 56,12250. |
| [11] | (c) Teichert,J. F.; Zhang, S.; Zijl, V.; Slaa,J. W.; Minnaard,A. J.; Feringa,B. L. Org. Lett. 2010, 12,4685. |
| [12] | Inubushi, Y.; Kikuchi, T.; Ibuka, T.; Tanaka, T.; Saji, I.; Tokane, K. J. Chem. Soc.,Chem. Commun. 1972,1252. |
| [13] | (a) Martin,S. F.; Li, W. J. Org. Chem. 1989, 54,268. |
| [13] | (b) Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2,3233. |
| [13] | (c) Padwa, A.; Brodney,M. A.; Dimitroff, M.; Liu, B. Wu,T. -H. J. Org. Chem. 2001, 66,3119. |
| [14] | (a) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1975, 97,6282. |
| [14] | (b) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1977, 99,1612. |
| [14] | (c) Roush,W. R. J. Am. Chem. Soc. 1978, 100,3599. |
| [15] | (a) Trost,B. M.; |
| [15] | (b) Sha,C. -K.; Chiu,R. -T.; Yang,C. -F.; Yao,N. -T.; Tseng,W. -H.; Liao,F. -L.; Wang,S. -L. J. Am. Chem. Soc. 1997, 119,4130. |
| [16] | (a) Brattesani,D. N.; Heathcock,C. H. J. Org. Chem. 1975, 40,2165. |
| [16] | (b) Kreis,L. M.; Carreira,E. M. Angew. Chem.,Int. Ed. 2012, 51,3436. |
| [16] | (c) Williams,B. M.; Trauner, D. J. Org. Chem. 2018, 83,3061. |
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